(1''S,3S,4''R,5'R,6''R,8''S,12''R)-1'',6'',8''-trimethyldispiro[bis(oxolane)-3,2':5',7''-[3]oxatricyclo[6.3.1.0^{4,12}]dodecane]-2'',5-dione

ID: ALA1079714

PubChem CID: 46883182

Max Phase: Preclinical

Molecular Formula: C20H28O5

Molecular Weight: 348.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@@H]1C[C@H]2OC(=O)[C@@]3(C)CCC[C@@](C)([C@@H]23)[C@@]12CC[C@]1(COC(=O)C1)O2

Standard InChI:  InChI=1S/C20H28O5/c1-12-9-13-15-17(2,16(22)24-13)5-4-6-18(15,3)20(12)8-7-19(25-20)10-14(21)23-11-19/h12-13,15H,4-11H2,1-3H3/t12-,13-,15+,17+,18+,19+,20-/m1/s1

Standard InChI Key:  UHVBVZOAJOXFRA-GBJBSKOPSA-N

Molfile:  

     RDKit          2D

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   -1.6667  -13.1152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8688  -13.3282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4195  -12.6352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9399  -11.9937    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7105  -12.2904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5027  -14.1557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7071  -13.9393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4383  -12.8238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9554  -13.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6396  -14.5733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6396  -15.3966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9254  -15.8081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9254  -14.1575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2153  -14.5733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2137  -15.3966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5051  -15.8054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7913  -15.3980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7887  -14.5706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7168  -16.5995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7365  -16.5698    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2107  -17.2623    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6480  -16.2155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2202  -16.2176    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0737  -14.1590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7923  -16.2180    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4065  -12.5912    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4341  -13.7698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  4  5  1  0
  5  1  1  0
  1  2  1  0
  6  7  1  0
  7  1  1  0
  1  8  1  1
  8  9  1  0
  6  9  1  1
 10 11  1  0
 10 13  1  0
 11 12  1  0
 12 15  1  0
 14 13  1  0
 14 15  1  0
 14  6  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18  6  1  0
 12 19  1  0
 19 20  1  0
 16 20  1  0
 19 21  2  0
 12 22  1  6
 15 23  1  6
 18 24  1  6
 16 25  1  6
  2  3  1  0
  3 26  2  0
  3  4  1  0
 14 27  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA1079714

   CID 46883182

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 348.44

Molecular Weight (Monoisotopic): 348.1937

AlogP: 3.00

#Rotatable Bonds: ┄

Polar Surface Area: 61.83

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.88

CX LogD: 2.88

Aromatic Rings: ┄

Heavy Atoms: 25

QED Weighted: 0.63

Np Likeness Score: 3.48

References

1. Rigano D, Aviello G, Bruno M, Formisano C, Rosselli S, Capasso R, Senatore F, Izzo AA, Borrelli F..  (2009)  Antispasmodic effects and structure-activity relationships of labdane diterpenoids from Marrubium globosum ssp. libanoticum.,  72  (8): [PMID:19650652] [10.1021/np9002756]

Source

Source(1):

• Scientific Literature